Ammonium Chloride → 1-Benzyl-4-bromoisoquinoline

HRID 42218

반응식

HRID 42218 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][N:3]=1.[Br-].[CH2:14]([Zn+])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[CH:4][N:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 4597664-Bromo-1-chloroisoquinolineHCID 178419772HCID 178419772, 화합물

생성물 1

HCID 236284181-Benzyl-4-bromoisoquinoline수율 25%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

In a 40 mL vial 490 mg (2.00 mmol) 1-chloro-4-bromo-isoquinoline and 40 mg (0.034 mmol) tetrakis(triphenylphosphine)palladium(0) is added to 4 mL THF. After all solids are dissolved, 8 mL of 0.5 M (4.0 mmol) benzyl zinc bromide in THF is slowly added by syringe and the resulting reaction mixture is stirred at 25° C. After 12 hrs, the mixture is poured into cold solution of saturated NH4Cl and extracted with EtOAc. The organic extracts are concentrated in vacuo and the resulting residue is purified by silica chromatography using a heptane/EtOAc gradient. Pure fractions are pooled and evaporated to give 150 mg (0.50 mmol) of the title compound.

후처리

  1. dissolutionAfter all solids are dissolved
  2. customthe resulting reaction mixture
  3. extractionextracted with EtOAc
  4. concentrationThe organic extracts are concentrated in vacuo
  5. customthe resulting residue is purified by silica chromatography
  6. customevaporated

출처 및 근거

ORD 기록
ord-219230f852f44f51bfb10fb2f15a93bf
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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